ChemSpider 2D Image | Phloretin | C15H14O5


  • Molecular FormulaC15H14O5
  • Average mass274.269 Da
  • Monoisotopic mass274.084137 Da
  • ChemSpider ID4624

More details:

Featured data source

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

1-Propanone, 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)- [ACD/Index Name]
200-488-7 [EINECS]
3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanon [German] [ACD/IUPAC Name]
3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone [ACD/IUPAC Name]
3-(4-Hydroxyphényl)-1-(2,4,6-trihydroxyphényl)-1-propanone [French] [ACD/IUPAC Name]
3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one [ACD/IUPAC Name]
60-82-2 [RN]

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

MFCD00002288 [DBID]
79310_FLUKA [DBID]
AIDS052153 [DBID]
AIDS-052153 [DBID]
C00774 [DBID]
CHEBI:17276 [DBID]
DivK1c_006429 [DBID]
EU-0101012 [DBID]
KBio1_001373 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      26-37 Alfa Aesar L10991
      36/37/38 Alfa Aesar L10991
      H315-H319-H335 Alfa Aesar L10991
      IRRITANT Alfa Aesar L10991
      IRRITANT Matrix Scientific 002894
      P261-P280-P305+P351+P338-P304+P340-P405-P501a Alfa Aesar L10991
      Warning Alfa Aesar L10991
      WARNING: Irritates lungs, eyes, skin Alfa Aesar L10991
    • Target Organs:

      SGLT inhibitor TargetMol T2924
    • Chemical Class:

      A member of the class of dihydrochalcones that is dihydrochalcone substituted by hydroxy groups at positions 4, 2', 4' and 6'. ChEBI CHEBI:17276,
      chalcone Microsource [00300554]
      Dihydrochalcones Phenol-Explorer 108
      Flavonoids Phenol-Explorer 108
    • Drug Status:

      undetermined activity Microsource [00300554]
    • Compound Source:

      Aegilops tauschii PlantCyc PHLORETIN
      Amborella trichopoda PlantCyc PHLORETIN
      Asparagus officinalis PlantCyc PHLORETIN
      Brachypodium distachyon PlantCyc PHLORETIN
      Cicer arietinum PlantCyc PHLORETIN
      Citrus clementina PlantCyc PHLORETIN
      Citrus sinensis PlantCyc PHLORETIN
      Corchorus capsularis PlantCyc PHLORETIN
      Dioscorea rotundata PlantCyc PHLORETIN
      Eucalyptus grandis PlantCyc PHLORETIN
      flavonoid di-C-glucosylation PlantCyc PHLORETIN
      Found in free state in Helichrysum splendidum Zerenex Molecular [ZBioX-0253]
      Fragaria vesca subsp. vesca PlantCyc PHLORETIN
      Glycine max PlantCyc PHLORETIN
      Gossypium raimondii PlantCyc PHLORETIN
      Helianthus annuus PlantCyc PHLORETIN
      Hordeum vulgare subsp. vulgare PlantCyc PHLORETIN
      Humulus lupulus var. lupulus PlantCyc PHLORETIN
      Leersia perrieri PlantCyc PHLORETIN
      Linum usitatissimum PlantCyc PHLORETIN
      Lotus japonicus PlantCyc PHLORETIN
      Malus domestica PlantCyc PHLORETIN
      Manihot esculenta PlantCyc PHLORETIN
      Marchantia polymorpha PlantCyc PHLORETIN
      Medicago truncatula PlantCyc PHLORETIN
      Miscanthus sinensis PlantCyc PHLORETIN
      Oropetium thomaeum PlantCyc PHLORETIN
      Oryza brachyantha PlantCyc PHLORETIN
      Oryza glaberrima PlantCyc PHLORETIN
      Oryza punctata PlantCyc PHLORETIN
      Oryza rufipogon PlantCyc PHLORETIN
      Oryza sativa Japonica Group PlantCyc PHLORETIN
      Panicum hallii PlantCyc PHLORETIN
      Panicum virgatum PlantCyc PHLORETIN
      Phaseolus vulgaris PlantCyc PHLORETIN
      phloridzin biosynthesis PlantCyc PHLORETIN
      Prunus persica PlantCyc PHLORETIN
      Prunus spp Microsource [00300554]
      Ricinus communis PlantCyc PHLORETIN
      Rosa chinensis PlantCyc PHLORETIN
      Rosa multiflora PlantCyc PHLORETIN
      Salvia miltiorrhiza PlantCyc PHLORETIN
      Selaginella moellendorffii PlantCyc PHLORETIN
      Setaria italica PlantCyc PHLORETIN
      Setaria viridis PlantCyc PHLORETIN
      Sorghum bicolor PlantCyc PHLORETIN
      Sphagnum fallax PlantCyc PHLORETIN
      Spirodela polyrhiza PlantCyc PHLORETIN
      Theobroma cacao PlantCyc PHLORETIN
      Trifolium pratense PlantCyc PHLORETIN
      Triticum aestivum PlantCyc PHLORETIN
      Triticum urartu PlantCyc PHLORETIN
      Vitis vinifera PlantCyc PHLORETIN
      Zea mays subsp. mays PlantCyc PHLORETIN
    • Bio Activity:

      4-dihydrocoumaroyl-CoA + 3 malonyl-CoA + 3 H+ -> phloretin + 3 CO2 + 4 coenzyme A PlantCyc PHLORETIN
      Antioxidant; Zerenex Molecular [ZBioX-0253]
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio HB0500
      Enzymes/Kinase/PKC Hello Bio HB0500
      Membrane Tranporter/Ion Channel MedChem Express HY-N0142
      Membrane Tranporter/Ion Channel; MedChem Express HY-N0142
      Membrane Transporter/Ion Channel TargetMol T2924
      Phloretin(NSC 407292; RJC 02792) is a dihydrochalcone, a type of natural phenols. MedChem Express, HY-N0142
      Phloretin(NSC 407292; RJC 02792) is a dihydrochalcone, a type of natural phenols. Phloretin inhibits the active transport of glucose into cells by SGLT1 and SGLT2.;IC50 Value: 49 +/- 12 microM [4];Target: SGLT1/2;In vitro: Phlorizin blocks glucose transport across the renal tubule at concentrations in renal blood and tissue in the range of 10-5 to 10-7 M [1]. PT significantly enhanced glycerol release and inhibited the adipogenesis-related transcription factors. PT also promoted phosphorylation of AMP-activated protein kinase and increased activity of adipose triglyceride lipase and hormone-sensitive lipase in 3T3-L1 cells [2]. Phloretin induced obvious cytotoxicity against BEL-7402 cells with IC50 of 89.23 microg/mL. The growth curve demonstrated decreased growth of the cells as phloretin concentration increased [3]. D-glucose-transport activity was observed with a Km for D-glucose of 3.4 +/- 0.2 mM (mean +/- S.E.M.) and was inhibited by cytochalasin B (IC50= 0.44 +/- 0.03 micr MedChem Express HY-N0142
      PKC inhibitor Hello Bio HB0500
      Protein kinase C (PKC) inhibitor. PGF<sub>2a</sub> receptor antagonist (IC<sub>50</sub> = 16 &micro;M). Inhibits GLUT2 glucose transport. Shows apoptotic, antitumor, antioxidant and immunomodulatory actions. Hello Bio HB0500
      SGLT MedChem Express HY-N0142
      SGLT1;SGLT2 TargetMol T2924
      UDP-alpha-D-glucose + phloretin -> nothofagin + UDP + H+ PlantCyc PHLORETIN
      UDP-alpha-D-glucose + phloretin -> phlorizin + UDP PlantCyc PHLORETIN
  • Gas Chromatography

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.4±0.1 g/cm3
Boiling Point: 534.4±29.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 84.1±3.0 kJ/mol
Flash Point: 291.1±20.8 °C
Index of Refraction: 1.685
Molar Refractivity: 72.9±0.3 cm3
#H bond acceptors: 5
#H bond donors: 4
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 0
ACD/LogP: 3.50
ACD/LogD (pH 5.5): 3.05
ACD/BCF (pH 5.5): 121.42
ACD/KOC (pH 5.5): 1071.89
ACD/LogD (pH 7.4): 2.53
ACD/BCF (pH 7.4): 36.66
ACD/KOC (pH 7.4): 323.64
Polar Surface Area: 98 Å2
Polarizability: 28.9±0.5 10-24cm3
Surface Tension: 74.9±3.0 dyne/cm
Molar Volume: 191.9±3.0 cm3

Predicted data is generated using the US Environmental Protection Agency�s EPISuite™

 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  3.51

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  467.47  (Adapted Stein & Brown method)
    Melting Pt (deg C):  197.40  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.26E-011  (Modified Grain method)
    MP  (exp database):  263.5 dec deg C
    Subcooled liquid VP: 5.16E-009 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  66.62
       log Kow used: 3.51 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  123 mg/L (16 deg C)
        Exper. Ref:  BEILSTEIN

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  960.61 mg/L
    Wat Sol (Exper. database match) =  123.00
       Exper. Ref:  BEILSTEIN

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.95E-016  atm-m3/mole
   Group Method:   7.39E-023  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  6.826E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.51  (KowWin est)
  Log Kaw used:  -14.098  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.608
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1417
   Biowin2 (Non-Linear Model)     :   0.9465
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7212  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.5200  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3138
   Biowin6 (MITI Non-Linear Model):   0.1709
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.0987
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  6.88E-007 Pa (5.16E-009 mm Hg)
  Log Koa (Koawin est  ): 17.608
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  4.36 
       Octanol/air (Koa) model:  9.95E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.994 
       Mackay model           :  0.997 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 205.0642 E-12 cm3/molecule-sec
      Half-Life =     0.052 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.626 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.995 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2.574E+004
      Log Koc:  4.411 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.159 (BCF = 14.43)
       log Kow used: 3.51 (estimated)

 Volatilization from Water:
    Henry LC:  1.95E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.973E+012  hours   (2.072E+011 days)
    Half-Life from Model Lake : 5.425E+013  hours   (2.26E+012 days)

 Removal In Wastewater Treatment:
    Total removal:              13.26  percent
    Total biodegradation:        0.19  percent
    Total sludge adsorption:    13.08  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       2.04e-006       1.25         1000       
   Water     11.6            900          1000       
   Soil      87.6            1.8e+003     1000       
   Sediment  0.86            8.1e+003     0          
     Persistence Time: 1.84e+003 hr


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